Molecular compounds of p-iodo-ethoxybenzoic acid benzylester



Patented Dec. 15, 1931 UNITED STATES ,oARn LUDWIG LAUTENsoHLAGEn, orFRANKZEORT-ON-THE-MAIN, MAX BocxMtrnL AND GUSTAV EHRHAR'D, OFHOOHST-ON-THE-MAIN, ADOL'F SCHWARZ, OF FRANKFORT-ON-THE-MAIN, GERMANY,ASSIGNOR-S, BY 'MESNE ASSIGNMENTS, TO

WINTHROIP CHEMICAL COMPANY, OF .NEW YORK, N. Y., CORPORATION OF NEW YORKMOLECULAR COMPOUNDS or P-IODO-ETHOXYBENZOIC. Acin B ENzYLnsTnn r V NoDrawing. Application filed April 15, 1926, seria noaioasoa,and inntrant, 4e25,:

The present invention relates to new name dies for diseases accompaniedby pathologic'ally increased blood-pressure.

It is known that medical science has for a long time endeavored to findtherapeutic means for reducing the pathologically increasedblood-pressure to its normal pressure or at least lowering it so muchthat the physical and psychical complaints of the patients are reducedto a minimum. The pharmacologists have made special eflorts to findsubstances which are capable of favorably influencing the hypertensionand the vascular spasms Without injuriously affecting the human body.Heretofore there have been chiefly used preparations of iodine andspasmolyticze, among the latter particularly preparations containing abenzyl radical. Furthermore, it has been proposed touse for the purposein question nitrites and nitro esters by which, however, no satisfactoryresults were obtained.

During the researches made in this highly important domain oftherapeutics it has been ascertained that the derivatives of hydrazoicacid, particularly its organic derivativesv have an extremely favorableaction on the hypertonic blood-pressure. In spite of their intensiveacting power it is, however, not advisable to use the azides alone,because their action is too fugacious owing to the fact that the saidazides degraded in the human body and are excreted too quickly.

We have during our own investigationsv made the remarkable observationthat it is possible to realize a much more favorable action than isobtainable by the heretofore plained by thef a'ct that the azides arecapable of entering into a molecular combination with the knownhypotonics. above mentioned for instance the benzyl derivatives orpurine .derivativesewhereby the distributing and excreting properties oftheazides are I naturally. largely. altered with the result that theazides obviously remain for a longer time in the human body..'

- For prepar i g the new therapeuticagents it is advantageousto'r'ender' the components homogeneous in'a finely subdivided state.

substance of particularlyhi'gh efficacy is obtained for instance bycombining one of the bodies described in German patent specification No.412,699 of July 30, '192 2,fwith pseudosaccharine" azide. The, favorableresults'obtained: by testing the new bodie's on l animals, havebeenfully confirmed by the observations madelwith human p atients.

' The following examples serve to illustrate our invention (-1) 1.91pa'rts ofp-iodoethoxybenioic acid A benzylester (see German patentspecification- No. 412,699)Land 1.04 parts of 'p'seudosac ch arineazideare" dissolved in 30' parts of acetone and the solvent-isevaporated in vacuo. (The remaining substance contains 9.5% of nitrogenand has the p robable for-I I mula:

oooomoum' v (lCzHJ i 1 1'; (2) In a melt, while it is still warm, of1.91 parts of p-iodoethoxybenzoic acid benzylester, are carefullydissolved 0.43 parts of carbamic azide. After cooling,the whole 1 masssolidifies into a colorless substance which has the probable formula:oooomom Nm-oom 011141 e (3) 2.02 9 parts of iod'odihyroxypropane and1.63 parts of p-hydroxybenzoic acidazide are dissolved in ether and thesolvent is then carefully evaporated. The product hastheprobableformulaf: V

CONa HOH dmon (4;) Into a solution, which has been prepared in the heatand then somewhat cooled, of 0.9 parts of theobromine in glacial aceticacid are introduced 1.02 parts of hippuric acidwazid'e. The solvent isthen carefully evaporated. The product has the probable V formula: 7

isrioo W V o ('30 d'N GsCaCONH-OHz-CON: I

sane Y 0.9 parts of theolo'romine a-nd 1.17 parts of fl naphthalenesulfonic acid azide are treated as, indicated in Example The v producthas the probable formula:

We claim:; I e 1. As new products, the molecular coinpounds consistingof p-iod0-ethoxyloenzoic acid benzylester and an organic azide, V 2. Asanew product, the molecularcompound consisting of ,p-iodo-ethoxyhenzoicacid benzylester and pseudo-saccharine azide.

' 3. Asa new product, the molecular C0111- pound consisting of about1.91 partsjof p- 40 iodosethoxybenzoic acid benzylester and about1.04parts of pseudo saccharine azide.

In testimony whereoflwe affix our signaf tures.v CARL LUDWIGLAUTENSCI-ILAGER. MAX BooKMuHL.

V GUSTAV EHRHART.

ADOLF SCHWARZ.

Certificate of Correction Patent No.1,836,125. Granted December 15,1931, to

CARL LUDWIG LAUTENSCHLAGER ET AL.

It is hereby certified that error appears in the printed specificationof the abovenumbered patent requiring correction as follows: Page 1,line 32, after the Word azides insert the Word are; page 2, after lines19 to 22 inclusive, strike out the formula and insert instead and thatthe said Letters Patent should be read With this correction therein thatthe same may conform to the record of the case in the Patent Office.

Signed and sealed this 7th day of June A. D. 1932.

[SEAL] M. J. MOORE,

Acting Commissioner 0 f Patents.

